International service learning programs have continued to rise in popularity across U.S. institutions of higher education as a way of offering students comprehensive formats to engage with communities in other countries, learn how social issues of inequality impact people around the world, and strengthen student learning on global issues. However, many of these programs lack a critical perspective, and often struggle or avoid conversations on the power dynamics of service, and, therefore, the potential harm that international service learning courses can cause and reproduce. At the same time, programs that do promote a critical approach to service abroad, fail to address the vital role that social identity plays in these programs (e.g., race, gender, sexuality, nationality, social class, etc.), and often ignore how those dynamics impact the differentiating experiences of students, and how they connect to the social issues community partners face. This dissertation study is an attempt to analyze a critical international service learning program to the Dominican Republic that I and a colleague co-led from 2018-2020. This program intended to offer intervention to both issues of critical awareness and identity dynamics through our integration of intergroup dialogue pedagogy and theory into all aspects of the program. Utilizing qualitative case study methods such as participant interviews, document analysis, and participant observations, I look at the impact that the 2020 version of the course had on 8 of the 11 students that year by analyzing their evolving learning in the areas of social identity, structural inequality, and service, as well as the program components that influenced this learning. Findings from the study overall suggest that participation in the program helped push students to reevaluate numerous aspects of their identity across areas such as race, gender, and SES/social class, and also better identify different forms of inequality and their impact – mostly in the context of the Dominican Republic and to an extent in the United States. With that said, learning outcomes were deeply tied to the positionality of students and their preexisting level of engagement with course themes. Generally, it seemed that students of greater racial and/or financial privilege were less willing to think critically about their positionality within systems of inequality and therefore their connection to the phenomena we observed abroad. This differed from students of less declared privilege who approached course materials through the intersection of social identity and inequality. Despite these gains, findings suggest that the course reproduced power hierarchies between our service group and community partners and within our group. Implications for research and theory include the need to further study the integration of intergroup dialogue in international service programs, the impact of greater community partner collaboration vis-à-vis dialogue and program involvement, and the exploration of increased affinity group work within service learning programs to better attend to student needs, especially those of students from marginalized positions.